Skip to main content
Log in

5-[5-R-furfurylidene]-2,2-dimethyl-1,3-dioxane-4,6-diones 6. Synthesis, structure, and properties of substituted furylimino- and furfurylidenephosphoranes. Molecular and crystal structure of N-[5-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl-2-furylimino(triphenyl)phosphorane

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Furylimino- and furfurylidenephosphoranes have been synthesized by sequential conversions of 5-unsubstituted and 5-methylfurfut),Iidetiedio.yanediones. The ylide fragment linked directly with the furfurylidenedioxanedione residue displays strong electron-donating properties, as a result of which resonance occurs in the system of conjugated bonds. The molecular and crystal structure of the iminophosphorane was studied by x-ray structural analysis and the resonance of the bonds in the molecule was confirmed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. G. D. Krapivin, N. I. Val'ter, T. Ya. Kaklyugina, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 3, 327 (1994).

  2. A. S. Tarasevich, I. E. Boldeskul, and V. P. Kukhar’, Usp. Khim.,55, 1344 (1986).

    Google Scholar 

  3. D. J. H. Smith, Comprehensive Organic Chemistry [Russian translation], Vol. 5, Khimiya, Moscow (1983), p. 96.

    Google Scholar 

  4. D. Vegh, J. Kovac, and M. Dandarova, Collect. Czech. Chem. Commun.,44, 1630 (1979).

    Google Scholar 

  5. I. N. Chernyuk, M. K. Bratenko, and M. I. Shevchuk, Zh. Obshch. Khim.,58, 306 (1988).

    Google Scholar 

  6. G. D. Krapivin, V. G. Kul'nevich, and N. I. Val'ter, Khim. Geterotsikl. Soedin., No. 10, 1325 (1986).

  7. G. D. Krapivin, V. E. Zavodnik, N. I. Val'ter, V. K. Bel'skii, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 11, 1453 (1988).

  8. G. D. Krapivin, V. G. Kul'nevich, and N. I. Val'ter, Khim. Geterotsikl. Soedin., No. 10, 1338 (1989).

  9. D. W. Cruikshank, Acta Crystallog.,17, 671 (1964).

    Google Scholar 

  10. N. G. Bokii, Yu. T. Struchkov, A. E. Kalinin, V. G. Andrianov, and T. N. Sal'nikova, Progress in Science and Technology. Crystallochemistry [in Russian], Vol. 12, All-Union Institute of Scientific and Technical Information (VINITI), Moscow (1977), p. 56.

  11. I. E. Mikhailov, O. E. Kompan, N. I. Makarova, A. I. Yanovskii, Yu. T. Struchkov, L. P. Oleklmovich, M. I. Knyazhevskii, and V. I. Minkin, Zh. Org. Khim.,21, 237 (1985).

    Google Scholar 

  12. G. M. Sheldrick, Computational Crystallography, Oxford University Press, New York (1982), p. 506.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 335–344, March, 1994.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Krapivin, G.D., Val'ter, N.I., Zavodnik, V.E. et al. 5-[5-R-furfurylidene]-2,2-dimethyl-1,3-dioxane-4,6-diones 6. Synthesis, structure, and properties of substituted furylimino- and furfurylidenephosphoranes. Molecular and crystal structure of N-[5-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl-2-furylimino(triphenyl)phosphorane. Chem Heterocycl Compd 30, 296–304 (1994). https://doi.org/10.1007/BF01165694

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01165694

Keywords

Navigation